114826-86-7

Basic information

• Product Name: (1R, 3S, 4R)-3-Benzyloxy-4-(benzyloxymethyl)cyclopentanamine
• Synonyms: (1R, 3S, 4R)-3-Benzyloxy-4-(benzyloxymethyl)cyclopentanamine
• CAS NO: 114826-86-7
• Molecular Formula: C₂₀H₂₅NO₂
• Molecular Weight: 311.42
• Mol File: 114826-86-7.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (1R, 3S, 4R)-3-Benzyloxy-4-(benzyloxymethyl)cyclopentanamine(CAS DataBase Reference)
• NIST Chemistry Reference: (1R, 3S, 4R)-3-Benzyloxy-4-(benzyloxymethyl)cyclopentanamine(114826-86-7)
• EPA Substance Registry System: (1R, 3S, 4R)-3-Benzyloxy-4-(benzyloxymethyl)cyclopentanamine(114826-86-7)

Safety Data

• Hazardous Substances Data: 114826-86-7(Hazardous Substances Data)

Usage

Uses

Used in Medicinal Chemistry:
(1R, 3S, 4R)-3-Benzyloxy-4-(benzyloxymethyl)cyclopentanamine is used as a building block for the synthesis of complex organic molecules, particularly in the development of pharmaceuticals. Its unique structure allows for the creation of diverse compounds with potential therapeutic applications.
Used in Pharmaceutical Research:
Due to its potential biological activity, (1R, 3S, 4R)-3-Benzyloxy-4-(benzyloxymethyl)cyclopentanamine is used in pharmaceutical research to explore its possible applications in medicine. Further studies may reveal its efficacy in treating various conditions or diseases, contributing to the advancement of healthcare solutions.
Used in Industrial Applications:
(1R, 3S, 4R)-3-Benzyloxy-4-(benzyloxymethyl)cyclopentanamine may also find use in other industrial applications beyond medicinal chemistry, given its unique chemical properties. Its potential uses could span across different sectors, pending further research and development.

Upstream product

• 1177260-52-4 tert-butyl ((1R,3S,4R)-3-benzyloxy-4-benzyloxymethylbicyclo[3.1.0]hexan-1-yl)carbamate 
• 100-39-0 benzyl bromide 
• 153045-91-1 tert-butyl-N-[(1R,3S,4R)-3-hydroxy-4-(hydroxymethyl)cyclopentyl]carbamate 
• 114924-87-7 (3R,3aR,4R,5S,6aR)-5-Benzyloxy-4-benzyloxymethyl-3-hydroxy-hexahydro-cyclopenta[b]furan-2-one 
• 76704-05-7 <3aS(3aα,4α,5β,6aα)>-(+)-5-hydroxy-4-hydroxymethyl-hexahydro-2H-cyclopentafuran-2-one 
• 114826-88-9 [(1R,2R,3S,5R)-3-Benzyloxy-2-benzyloxymethyl-5-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hydroxy-acetic acid methyl ester 
• 114826-90-3 (1S,2R,3S,5R)-3-Benzyloxy-2-benzyloxymethyl-5-(tetrahydro-pyran-2-yloxy)-cyclopentanecarbaldehyde 
• 114826-91-4 (1S,2R,3S,5R)-3-Benzyloxy-2-benzyloxymethyl-5-(tetrahydro-pyran-2-yloxy)-cyclopentanecarboxylic acid 
• 114826-89-0 1-[(1R,2R,3S,5R)-3-Benzyloxy-2-benzyloxymethyl-5-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-ethane-1,2-diol 
• 114826-92-5 2-((1R,3R,4S)-4-Benzyloxy-3-benzyloxymethyl-2-iodo-cyclopentyloxy)-tetrahydro-pyran 
• 114826-84-5 (1S,2R,3S,5S)-5-Azido-3-benzyloxy-2-benzyloxymethyl-cyclopentanecarboxylic acid 
• 114826-93-6 2-((1S,3S,4R)-3-Benzyloxy-4-benzyloxymethyl-cyclopentyloxy)-tetrahydro-pyran 
• 114826-83-4 (1S,2R,3S,5S)-5-Azido-3-benzyloxy-2-benzyloxymethyl-cyclopentanecarbaldehyde 
• 114846-99-0 (1R,2S,3R,4S)-4-Benzyloxy-3-benzyloxymethyl-2-(2,2-dimethyl-[1,3]dioxolan-4-yl)-cyclopentanol 

Downstream Products

• 114884-15-0 1-((1R,3S,4R)-3-hydroxy-4-(hydroxymethyl)cyclopentyl)-5-methylpyrimidine-2,4(1H,3H)-dione 

Relevant articles and documents

CARBOCYCLIC NUCLEOSIDE ANALOGUE

The present invention relates to novel hydrolytically stable carbocyclic 5-aza-2-deoxycytidine and carbocyclic 5-aza-cytidine compounds and prodrugs thereof as hypomethylating agents.

Influencing Epigenetic Information with a Hydrolytically Stable Carbocyclic 5-Aza-2′-deoxycytidine

5-Aza-2′-deoxycytidine (AzadC) is an antimetabolite in clinical use, which reduces the level of the epigenetic modification 5-methyl-2′-deoxycytidine (mdC). AzadC is incorporated into the genome of proliferating cells, where it inhibits DNA methyltransferases (DNMTs), leading to a reduction of mdC. The loss of mdC, which is a transcriptional silencer in the promoter region found upstream of genes, leads to the reactivation of the corresponding gene, including tumor-suppressor genes, which elicits a beneficial effect. The problem associated with AzadC is that the compound is hydrolytically unstable. It decomposes during treatment to a variety of poorly characterized hydrolysis products. After its incorporation into the genome, this hydrolytic instability generates abasic sites. It is consequently difficult to dissect whether the activity of the compound is caused by DNMT inhibition or more generally by DNA lesion formation. We now discovered that a disarmed version of AzadC, in which the ribose oxygen was replaced by a CH2 group, is surprisingly stable under a variety of pH values while keeping activity against the DNMTs.

New convergent synthesis of carbocyclic nucleoside analogues

Two convergent approaches towards the synthesis of carbocyclic nucleoside analogs will be described. Both approaches start from the stereochemically pure cyclopentenol 8 that has been prepared enantioselectively from an alkylated cyclopentadiene. Using these approaches, carbocyclic analogues of dT, FdU and BVdU have been prepared. Moreover, the conversion into the cycloSalpronucleotide and the corresponding nucleotide will be presented for one example.